To a stirred mixture of 3.5 g (0.0887 mole) of a 60% suspension of sodium hydride in hexane in 50 ml of DMF was added 18.1 g (0.0721 mole) of 4-(4-methoxybenzoyl)indole. The mixture was treated with a solution containing 0.18 mole of 4-(2-chloroethyl)morpholine in t-butyl methyl ether (prepared by extraction of the free base from a suspension of 35.5 g of the corresponding hydrochloride in saturated sodium bicarbonate). When addition was complete, the reaction mixture was heated under reflux for about twelve hours, treated with 1500 ml of water and extracted with 500 ml of ethyl acetate. The combined organic extracts, on drying and evaporation to dryness, afforded an oil which was dissolved in 250 ml of ethyl acetate and treated with 50 ml of ethereal hydrogen chloride. The material which separated was collected and recrystallized from ethanol to give 20.3 g of 4-(4-methoxybenzoyl)-1-[2-(4-morpholinyl)ethyl]-1H-indole hydrochloride, m.p. 177°-180° C.
